Settings for using Outlook/Hotmail SMTP via Gmail

Thanks for pursuing this with me, Diane. 

OK, so come Sept., oAuth2 will work with gmailify (don’t really know what that is, I hope it is automatic, or that we get the info we need to set it up). 

RE the current issue:

OK, I now see that “Manage how you sign in to Microsoft page.” And there is it using the “primary account” term, unlike the previous page. See my page below. And you can see I have the primary account under “hotmail.com.” I have been allowed to make aliases only as “outlook.com” addresses. 

In my insert below, see the bottom, where I have put in an arrow pointing to a link to “Change sign-in preferences.” I clicked through to that, and the page that comes up, second insert, provides for allowing login to any or all alias accounts; the primary account is check on by default, and cannot be turned off. (I had not seen the link leading to the second insert previously, so now more info is at hand for this.)

As you see, all my aliases are checked on, to allow sign-in through them. And in the past, I had set them up and used them from Gmail without this issue that arose some months back, the issue of it not sending from gmail, I have to instead go to hotmail to send via the alias. The gmail SMTP use of that to log in under a particular alias is being rejected, despite my second insert below showing I have turned on the function to allow login via that alias. And again, I have been able to send from gmail in the past. 

I would think allowing sign-in via an alias would include signing in via SMTP to allow that pass through. This is the problem now, it is blocking that. Has Microsoft intentionally done something some months back to stop allowing that? I have tested, and I can still sign into my Hotmail account using my alias to do so instead. 

(Strange system to making an insert, but it works.)

Before I address your specific questions - to add to my previous comments that this will stop working in September. I tried gmailify option. It uses oAuth2 and will work after Microsoft turns off basic auth in September. The only issue is that it only supports one account.

Your primary is at the top of the alias list in outlook.com - that is the address you need to use in gmail.
https://account.live.com/names/manage

This is what worked for me - for smtp - but because this uses basic auth, it will stop working in September.

Thank you, Diane. I see no place in my Hotamil account where any address is designated as "primary." But the one that I would designate as such is instead marked as the one I log in with. In reality, I have tested in the past, and just now with the alias in question, and I can log into the account with any of the aliases, using the same password as for my primary account designated as the one I log in with.

In Gmail, none of those aliases are designated as "primary." However, the primary one is designated as the default.

I don't seem to have the problem when using the default address, which is my primary address, as I do with the alias. The default is set up as:

•SMTP server, the default addres uses: hotmail-com.olc.protection.outlook.com.

•User Name, the default address uses the moniker on the account before @hotmail.com. For example, if it were ******@hotmail.com, the User Name in the setup is merely name4321, not ******@hotmail.com.

I note, the alias I am having trouble with is @outlook.com. It doesn't seem to matter if I do or do not add the @outlook.com as the User Name.

My mutiple aliases all used to work fine. I have a few others, but I'm only using the one now. It now has the probiem, that started some months back, it works only if I use it directly from Hotmail, not from my Gmail account. My default hotmail account works fine out of my gmail account. So, maybe what you said is so, but I note again, they all used to work out of gmail"

"Some clients can only connect with the primary address on the account."

>>

My user credentials are the e-mail address I have set up in my Hotmail as an alias. I'm using the correct password, I log in every day with it.

I just thought of one detail I might not have mentioned. Once we send like that, it goes to the receiver from the alias e-mail address.

>>

Some clients can only connect with the primary address on the account. If a non-Microsoft address is primary, try setting Hotmail as primary and see if it works.

I haven't tried gmailify so maybe it works with oAuth2 - but the pop connection does not. It's possible Gmail will update it to use oAuth2... but I'm not hopeful that will happen.

Thank you, Edouard Imbert. But I've already tried that, as notied somewhere above. It doesn't work for me. And as I noted somwhere above, I'm not using it via a phone app, I'm using it online from my computer. I did try 2-step verification, and got the password from that, it just did not fix the issue.

But gee, it hardly matters now, since Diana P above points out that Microsoft will be disabling basic authorization come Sept., and Google apparently doesn't offer that, so we all will be cut off from doing this. She did hedge her comments, maybe that not happen.